Synthesis, characterization, X-Ray crystal study and bioctivities of pyrazole derivatives: Identification of antitumor, antifungal and antibacterial pharmacophore sites

The reaction of hydroxymethyl pyrazole derivatives with one equivalent of the appropriate primary amine yields N-((1h-pyrazol-1-yl) methyl) pyrimidin-2-amine (L1), 2-(((1h-pyrazol-1-yl) methyl) amino) benzoic acid (L2), and ethyl 5-methyl-1-(((6-methyl-3-nitropyridin-2-yl) amino) methyl)-1h-pyrazole-3-carboxylate (L3). The structure of synthesized compounds (L1-L3) was identified by FT-IR, UV–visible, proton NMR spectroscopy, mass spectroscopy, and single crystal X-ray crystallography. The armed pyrazoles (L1-L3) were crystallized in the space groups C2/c, P21/n and P-1 for L1, L2, and L3 respectively. Crystallographic analysis revealed that N–H of the amine group and Nitrogen or Oxygen atoms are in-plane with the aromatic ring. The aminomethyl chain forms a distorted second plane. The angle between the two planes is observed to be 76.07° (N2–C7–N5–N19) for L1, 62.12° (N34–C63–N22–N35) for L2, 60.84° (N3–C8–N2–N1), and 0.41° (N1–C4–C3–O1/O2) for L3 was studied. Theoretical physical and chemical properties calculations have been performed on the studied armed pyrazoles (L1-L3) using three different programs: Petra, Osiris, & Molinspiration (POM). The geometric parameters of the optimized structure are in agreement with the experimental data obtained from the X-ray structures. The origin of the biological activity against breast cancer and microbes has also been confirmed. [Display omitted] •The antitumor, antimicrobial activity of novel armed pyrazole derivatives was evaluated.•Identification of potential combined antimicrobial/antitumor pharmacophore sites by crystallographic analyses.•Computed quantum chemical descriptors based upon POM calculations have been used to correlate with biological activity.